1. a few of your items are rather dated and/or reflect an immature view of menswear. For example, blue shirt, contrast white cuff/collar. Meh, was popular in the 80's and guys who don't know better think they're "spiffy". Your last blue shirt, the darkish blue one I think is French blue, something that was popular around the mid 90's. Your black shirt, unless you're wearing it out for a night on the town or something, it's a toss. Your darkish green shirt, donate. Dark red and dark red checks are business casual, which is fine, but those colors are a bit too flashy. Generally shirts should be lighter than the tie or suit/sportscoat. If you're doing patterns, either make them very simple or small, or simple and large scale. Bright colors are a no go until you've mastered the basics. Start with white, blue in all sorts of patterns, and add in some skin tone appropriate variations like very light - pink, purple, green, yellow, and really these are pretty far down the list. the half zips were popular, but like 10ish years ago? maybe a bit less, but they're very "banana republic IT guy".
2. Resist the urge to go for the extremes, the bright colorful stuff, the dandy, the fun thing you saw on the cover of GQ, that thing your father always did, etc. Start with simple solid basics and work from there. Fit is king. Find your voice through the subtle details of shape, proportion, fabric texture, pattern, etc. Start there. Color is one of the last stages because it's so easy to go overboard. And if you have something that calls attention, then make everything else around it neutral and restrained so it doesn't go over the top. I've seen this happen over and over again with middle aged to older guys. They have a dated view of menswear from the 80's where it was big bold over the top or they have Astaire aspirations or something and they focus on all the crazy wild fun 'visual interest' stuff instead of getting the basics right.
3. ignore brands, focus on fit. You've listed off a stack of brands like they're a high and low list and will earn you credibility with the community. is "Brooks Brothers, Loro Piana weather system" supposed to help me? How about a fit picture so I know if it even makes sense? Learn about fabric, fit, construction (it's overrated IMO), and what works for you. Don't get so hung up on this or that brand and having the 'right' ones. Learn to understand if an item is right for you, and then figure out if it's worth the asking price. I have a total mixed bag of low to high end brands and mix them fairly consistently. Brands imply something, but if you have your own voice, that's what'll come through. Guys who really know their own taste just go MTM/Bespoke. They don't bother with brand this or that, just the styling. Get to know your tailor (find a good one) and tailor things if necessary. Of course, don't buy it if it doesn't work, but within reason. A tailor will take a $20 shirt and charge you $25 and you're left with a $200 MTM looking shirt.
4. Find what really works for you, not what you see or like or want to try. Don't waste time, money, and energy on the excess stuff early on. Focus on the core elements and learn your body shape, style preferences, realistic needs, etc. So for example, do you need white linen pants? does a light bottom and dark top work for your frame? Think more about cuff size, lapel width and pant length. Don't focus on pocket squares just yet, or colorful socks. Those are the excesses that brighten up a solid foundation. Keep it simple and solid. Your priorities should be on fit and solid basic pieces that you'll get a lot of use out of. Start there.